Reluctantly Agree

Dammit, you don't want this. Anal sex isn't what you signed up for, and no matter how Cassie rationalizes it away, it's kinda gay, letting someone, man OR woman, stick a cock up your ass. But ...

But like it or not, you've given up control of your relationship, and as long as you want to continue with this fulfillment of your chastity kink ... and you DO ... you're not getting it back.

But she said the two of you are coming right back here ... to her giant, pink dildo, anal sex, and your ass ... again and again until you agree to ... let her ... fuck you in the ... ass ...

But you really, really need to cum. Soon. No, now.

But ... what if you discover you ... like it?

You close your eyes. You don't want to look at her while you say this. "Okay, go ... go ahead."

Her hand touches your spine between your shoulder blades, and slides down towards your hips while she speaks, "Oh, Chasty. You ought to know better than that by now. How does my little slut-boi ask for sex favors?"

Favors?! You wonder for a split second whether Cassie has actually lost her mind before you realize that she's just playing her self-defined dominant role, enjoying the control you've given her. And you're going to play along to get past this to somewhere that she might touch you, or better, someday let you dip your wick again.

"Please, Cassie ... please ... make me cum. I need it so bad, baby. Please?"

"What do you need 'so bad,' babe? Tell me."

You grit your teeth, but manage to get the words out. "Please use Mister Pink on me? Fuck my ass?"

"Good boy," she says, patting your cheek, "We're gonna have to talk about an extra 'price' for letting you cum, and make THAT your 'indecision tax' instead of the eighteen-day wait, but I'll be happy to give you that anal climax, baby."

She lies down on the bed in front of you, Mister Pink between you, and holds it up to your lips. "Kiss it," she orders, "Kiss the tip."

Aghast, you turn your head and pull away, but she follows you with the big, bright pink thing. "Come on, Chasty. You gotta show some respect when something ... or someone ... gives you pleasure. Before or after, I don't care, but you're GOING to kiss it."

Faced with the prospect of kissing the thing AFTER it's been in your bowels, you slowly, oh-so-hesitantly pucker up and kiss the dildo's tip.

"Gooooood boy," she croons, smiling before kissing you and sliding her knee between yours, sliding upwards until she's rubbing your balls with her thigh. She gives you another quick peck before turning away for a moment and taking a small bottle of Astroglide from the box that had contained the dildo. She drips a few droplets of the lube on the head of the rubber cock, and begins to coat the head and shaft with her hands. That done, she wraps her arms around you, pressing her body to yours, her stiff nipples rubbing against yours, her belly warm against you. You've been excited since the day started; that's why your in this position. But now your cock is trying to get so hard inside its cage that it hurts. You groan desperately.

"Oh, baby," Cassie croons in your ear, slipping the dildo between your ass cheeks, "I am gonna make you cum so hard, you won't believe it."

She presses the cockhead against your sphincter muscle. "Nice and easy, now, baby," she says, "Try to relax back there, okay?" She presses just a little harder against your back door.

You do try to relax "back there," but it's hard; your first instinct is to tighten up, to expel the phallic latex invader. The experience isn't really painful; the slow steady pressure just slowly grows over the next few minutes, but the feeling of your sphincter stretching and your anus filling is ... weird, and a little uncomfortable.

Then the cockhead enters your rectum.

At first it's just a "full" sensation behind your bladder, as though you need to take a dump. But then ...

"Oh, my God!"

You don't say it, because suddenly all you can make is vaguely animalistic grunting noises. But that's what you're thinking. In fact, that's all you CAN think for a moment, while the stimulation inside you makes your penis suddenly twitch and jump in its attempts to grow inside its plastic prison.

Cassie pushes a little harder, filling your rectum and making the latex invader rub against the sensitive gland. "Like that, do you?" she chuckles.

Still not quite able to form human words, you simply nod, panting. She kisses you again, humping your leg while she begins, slowly, to pull the cock in your ass back out. You hear a quiet whine escape your lips as your rectum empties.

Cassie does this a half dozen times, in and out, a little faster every time. You're barely noticing the streyched feeling in your sphincter now, and you find yourself pressing back against her every time she presses the dildo into you to increase the stimulation as it rubs your prostate, Cassie encouraging you, until you're moving like you're fucking her rather than getting fucked. Soon you've lost count of how many times she's thrust the thing into you.

Your climax, when it comes, is the most powerful experience you've ever had. It starts as a sort of pressure in your solar plexus, belly and balls, one that grows and grows until it fills your mind. Then, suddenly, it releases, and all of that tension just sort of flows out of you through your cock as you spurt again and again, covering Cassie's legs and belly in what feels like a gallon of cum. Your eyes actually roll back in your head for a moment.

When you open them again, Cassie is kissing you and your backside feels ... strangely empty. You look down in some embarrassment, to see that what had felt like a gallon of cum is actually maybe an ounce or two. Cassie smiles at you and, reaching down, wipes up some of your spend and presses it to your lips. You don't exactly welcome it, but you're too worn out to pull away before she's stuck her finger in your mouth, sliding the slimy, salty substance across your tongue.

"Feel better?" she asks, smiling at your nod.

"Good. Maybe next time, you'll trust me a little," she replies, rising from the bed and grabbing a tissue to wipe herself with, "Speaking of which, now it's time to pay the price ... both for your fun and for not just trusting me."

She picks up her purse and removes what looks like a gift box from a high-end lingerie store. "I've been planning for this, Chasty, but I'd hoped I could let you choose. Now, I'm afraid I'm going to have to bring your testosterone-fueled 'little Chasty' under control. Open the box, baby."

You do so. Inside are a ... TINY is the only appropriate word for it ... stainless steel chastity device, a smallish butt plug, and a pair of pink, lacy ladies' panties. You look at her in shock and dread.

"I'd HOPED to let you choose ONE today, as I said. But now I think it's time to fit you for the size-small chastity. YOU get to choose one of the others to wear from now on ... your 'indecision tax.'"

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